Ammonium Chloride → HCID 22288509, compound

HRID 968220Notes

Reaction equation

HRID 968220 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=[C:4]([NH2:16])[C:3]=1[N+:17]([O-])=O.[NH4+].[Cl-]>CCO.O.[Fe]>[Cl:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=[C:4]([NH2:16])[C:3]=1[NH2:17]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 22288477HCID 22288477, compound

Product 1

HCID 22288509HCID 22288509, compoundYield 78.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of the product from example 2, step (d) (980 mg), NH4Cl (1.61 g) and iron powder (559 mg) in EtOH (100 ml) and H2O (15 ml) was heated at 85° C. for 1.5 h. The mixture was filtered through celite and washed with hot MeOH (100 ml) before concentrating the filtrate onto silica under reduced pressure. Column chromatography using 1:1 isohexane/ethyl acetate as eluent provided the subtitled product as a yellow solid (0.69 g, 78%)

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed with hot MeOH (100 ml)
  3. concentrationbefore concentrating the filtrate onto silica under reduced pressure

Sources & evidence

ORD record
ord-773b4529c11144678cc511dc912c6f38
Source dataset
uspto-grants-2005_10
Patent number
US06958344B2

Reaction notes

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